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Family-friendly holiday rentals in Cupertino

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Cupertino

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Cabin in Los Gatos

4.9 out of 5 average rating, 440 reviews

The Coach House

The Coach House is located on our mountain top horse and lavender farm. We offer youth summer camps so are set up for fun outdoor adventures and activities. Have fun with our horses, goats, and chickens! You can take a 10 min walk over to Nonno's Restaurant for wine/pizza/BBQ and bacchi ball, or take an 8 min drive into Los Gatos, or 15 min to Santa Cruz for the beach and some of the best restaurants and spas around!. Good for couples, solo adventurers, business travelers, kids, & behaved dogs!

Guest favourite

Home in Portola Valley

4.93 out of 5 average rating, 146 reviews

3 BR Home on Vineyard nr Palo Alto & Stanford

Professionally cleaned detached home nestled among an oak grove, waterfall & vineyard in the hills above Stanford (10 min), Palo Alto (20 min), Menlo Park (10-20 min), Mountain View (25 min) and San Francisco and San Jose. Perfect for families and groups; staycations, off-sites or startups visiting Silicon Valley . See resort-style amenities below. LATEST UPGRADES: better AC, faster internet & WiFi6 for lots of devices & bandwidth. Pickleball lines on tennis court; putting green w/ remote tees.

Guest favourite

Home in San Mateo

4.84 out of 5 average rating, 205 reviews

Quiet 3ba/2ba HOUSE with backyard orchard. 🏡

For Business or Leisure. Comfortable place with easy check in with a team, smart choice over hotel. Beautiful 3 bedrooms home in nice neighborhood of San Mateo in the heart of Silicon Valley. 10 mins to SFO, 7 mins to Cal Trains, 11mins to BART train. A convenient location just a short hop to San Francisco and Palo Alto. Walk to the beach, running trail with breathtaking bay view, tennis court. Open to long term furnished rental. All 3 bedrooms with premium queen beds and mattresses. New Sofa

Home in Foster City

4.86 out of 5 average rating, 179 reviews

❤️ Amazing! 2B/2B with a leisure garden.

Beautiful and comfortable end-unit, step-free, single-level townhouse with 2 bedrooms and 2 full baths. This corner unit opens up into a beautiful garden. located between San Francisco and Silicon Valley. A full kitchen, central heating, and washer/dryer are in the house. garage parking. backyard and patio. Few minutes walking distance to parks, restaurants, and the seaside walkway. It's excellent for vacations as well as business and professional stays. Check yourself in with the keypad code.

Home in Ben Lomond

4.93 out of 5 average rating, 132 reviews

Central Coast; Meadow, Hot Tub, Polite Pets Welcom

VR#111596 Seemingly remote & private yet so close to everything, single level home with massive deck on 2 1/2 acres backs to park and trails. The cook’s kitchen & herb garden overlook our meadow. The hot tub, outdoor living room & garden shower are just a few of the surprises you will uncover. The 350 heritage oak tree with 10,000 sq ft canopy is a magnet for wildlife. Ask about detached office if you need to work from home; the internet is great. Polite well trained pets OK.

Guest favourite

Townhouse in Pleasanton

4.88 out of 5 average rating, 376 reviews

Great Townhouse in charming Pleasanton

3 bed 1.5bath townhouse with 1 car garage. Fully furnished with beautiful high end but cozy furnishings. Max guests are 6 adults 1 infant no extra guests. 1 cal-king, 1 queen, 2 twin beds. Please be advised there are stairs and some people say they are steep. Smart TVs YouTube TV Netflix etc. High speed Wi-Fi internet is included. The house has central heating and air conditioning and is professionally cleaned before every booking. Home comes fully stocked with everything you need.

Guest favourite

Home in Livermore

4.94 out of 5 average rating, 378 reviews

G & M #1 Livermore Wine/ E-Bike Getaway (Pets ok)

E-Bikes Hot tub fire pit 1 Queen bedroom 1 double bedroom 1 futon 1 bath, fully furnished with all amenities needed. wi/fi ( Pets ok $20.00 per pet per stay Please notify at booking), washer dryer on site. Includes country breakfast fixings you cook it (or) continental breakfast for first morning breakfast. Located with our small family vineyard in the back of the property. Wineries and downtown Livermore 5 min by car. many different farm animals on property for you to visit.

Home in Brisbane

4.9 out of 5 average rating, 101 reviews

Luxurious Bayview Treehouse: Hot Tub, 15 min to SF

Immerse yourself in an architectural gem that balances modern elegance and rustic allure. Our four-bedroom, three-bathroom sanctuary is your secluded escape amidst expansive greenery, a canvas for unforgettable moments. Just 10 minutes from SFO Airport and 15 minutes from dynamic San Francisco, our home is your launchpad to exploration. The Bay Bridge graces the view from your private balcony and hot tub, framing your stay with an awe-inspiring vista.

Guest favourite

Guest house in Monte Sereno

4.9 out of 5 average rating, 206 reviews

Greenwood Guest House, a Peaceful Oasis

Welcome to Greenwood Guest House, a 1 bedroom, 1 bath private house situated in a peaceful and expansive backyard with a pool, tennis court, and beautiful scenery. Our space is a good fit for business trips, couple vacations, and family visits. The kitchenette and laundry room make longer stays quite enjoyable. Easy access to Highway 17 and 85, 15 minute drive to San Jose airport (SJC) and 2 minute drives to either downtown Los Gatos or Saratoga.

Home in Mountain View

4.84 out of 5 average rating, 285 reviews

Cute two bedroom home in fantastic location!

Cute, cozy remodeled duplex in a great neighborhood with a fenced in yard and surrounded by parks. The amazing location...You have access to 3 freeways, and Central Expressway. This means in 15 minutes by car you can be in S tanford, Los Altos, Palo Alto, San Jose, Milpitas or the east bay. By foot or bike you can reach beautiful shoreline park, two public rail systems, and lovely downtown Mountain view with great food!

Guest favourite

Guest suite in San Jose

4.91 out of 5 average rating, 231 reviews

Cozy,Quiet”Home Away from Home”.attached cottage

Very large 1 bedroom. Heat/AC, Private entry, Loaded with Amenities. Private Patio, Garden View, parking in front. Nice, Quiet neighborhood; near trails, Pond, Freeways, Light Rail(VTA). 10 min walk to Westfield Oakridge Mall, Restaurants/Movies, Bowling, Mini golf, Walmart, Costco, Bass Pro, and much more. 1 HR to SFO/Monterey 30 Min to Santa Cruz Beach/Gilroy Outlets 20 Min Dwntwn SJ/SJSU

Guest favourite

Flat in Brisbane

4.86 out of 5 average rating, 457 reviews

Exceptional Value-close to SFO, Welcome Valkyries!

Brisbane/ San Francisco This apartment is cleaned and sanitized between guests. Guests are required to accept and follow State and local regulations. We are a 10 minute drive from San Francisco Airport, 20 minutes from downtown San Francisco. Free street or on-site parking. Bedroom area, living room area, galley kitchen, and bath. Free Wi-Fi, cable TV, and Netflix

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Popular amenities for Cupertino family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest favourite

Guest suite in San Carlos

4.81 out of 5 average rating, 187 reviews

Sweet Studio -SF Peninsula

Cabin in Felton

4.91 out of 5 average rating, 488 reviews

Tranquility Base Redwood Mountain Tree House

Guest favourite

Home in Redwood City

4.97 out of 5 average rating, 297 reviews

Private suite

Guest favourite

Villa in Monte Sereno

5 out of 5 average rating, 36 reviews

Los Gatos Villa: hot tub, sauna, pool, huge yard

Guest favourite

Home in Burlingame

4.97 out of 5 average rating, 160 reviews

SFO Panoramic Views 4BR/3BA near SF-Silicon Valley

Guest favourite

Home in East San Jose

4.93 out of 5 average rating, 247 reviews

Gr8View-LrgDeck-BBQ-Spa-PoolTable-2xOven-Sleeps12

Guest favourite

Apartment in Mountain View

4.95 out of 5 average rating, 130 reviews

Spacious Top Floor Condo Retreat

Guest favourite

Apartment in Santa Clara

4.94 out of 5 average rating, 300 reviews

La Casa de Alpaca

Family- and pet-friendly home rentals

Guest favourite

Home in San Jose

4.92 out of 5 average rating, 384 reviews

Comfortable Whole Home on two house lot

Guest favourite

Train in Cupertino

4.92 out of 5 average rating, 388 reviews

Caboose in the redwoods just outside of Cupertino

Townhouse in San Jose

4.85 out of 5 average rating, 104 reviews

Santana Row Luxury Condo 2 Story 1100 Sq Feet

Guest favourite

Guest house in Menlo Park

4.97 out of 5 average rating, 149 reviews

Cottage near dwntwn Palo Alto, Stanford, Face-book

Guest house in Monte Sereno

4.84 out of 5 average rating, 159 reviews

Private Cozy suite Los Gatos -Saratoga

Guest favourite

Guest suite in Campbell

4.95 out of 5 average rating, 399 reviews

Cottage - bedroom, living, bath and small kitchen

Guest favourite

Apartment in San Jose

4.88 out of 5 average rating, 210 reviews

Santana Row Properties #2 - Silicon Valley Getaway

Guest favourite

Guest suite in Woodside

4.88 out of 5 average rating, 371 reviews

Stay Nestled in Ancient Redwoods in Silicon Valley

Family-friendly home rentals with a pool

Home in Union City

4.88 out of 5 average rating, 103 reviews

Impressive Exec. Luxury Home, Pool & SPA, Central

Guest favourite

Home in Menlo Park

4.89 out of 5 average rating, 54 reviews

Mission style, w. Pool, Hot tub, walk to downtown

Guest suite in Boulder Creek

4.93 out of 5 average rating, 67 reviews

Magical Huckleberry Woods Sanctuary w/Pool and Spa

Home in Santa Clara

4.81 out of 5 average rating, 37 reviews

Modern Retreat in the Heart of Silicon Valley

Home in Santa Clara

4.67 out of 5 average rating, 3 reviews

Modern Rivermark Home near tech companies

Flat in San Jose

4.75 out of 5 average rating, 67 reviews

2 BR/2 full bath Modern Santana Row Condo sleeps 6

Home in Berryessa

4.62 out of 5 average rating, 127 reviews

Serene, Large 4BR/2.5BA Home in San Jose

Quick stats about holiday rentals that are family-friendly in Cupertino

Total rentals
120 properties
Nightly prices starting at
₹3,464 before taxes and fees
Total number of reviews
3.4K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
70 properties have a dedicated workspace

Destinations to explore